US3943122A - Polyazo compounds containing benzhydrol as a component - Google Patents
Polyazo compounds containing benzhydrol as a component Download PDFInfo
- Publication number
- US3943122A US3943122A US05/217,950 US21795072A US3943122A US 3943122 A US3943122 A US 3943122A US 21795072 A US21795072 A US 21795072A US 3943122 A US3943122 A US 3943122A
- Authority
- US
- United States
- Prior art keywords
- parts
- dyestuff
- azo
- formula
- nitro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 Polyazo Polymers 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 title description 7
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 7
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
- 102100021464 Kinetochore scaffold 1 Human genes 0.000 claims 1
- 101710180647 Proprotein convertase subtilisin/kexin type 7 Proteins 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 description 23
- 230000008878 coupling Effects 0.000 description 22
- 238000010168 coupling process Methods 0.000 description 22
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 12
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 11
- 239000010985 leather Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LVYZWDOXAIFVRX-UHFFFAOYSA-N 4-[hydroxy(phenyl)methyl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1C(O)C1=CC=CC=C1 LVYZWDOXAIFVRX-UHFFFAOYSA-N 0.000 description 6
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 244000309466 calf Species 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000009963 fulling Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical class C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- ILIRBCKZTLSMQZ-UHFFFAOYSA-N 2-[[5-benzoyl-3-[(2-carboxy-4-sulfophenyl)diazenyl]-2,4-dihydroxyphenyl]diazenyl]-5-sulfobenzoic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1N=NC1=CC(C(=O)C=2C=CC=CC=2)=C(O)C(N=NC=2C(=CC(=CC=2)S(O)(=O)=O)C(O)=O)=C1O ILIRBCKZTLSMQZ-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- FWBBZLMJJAUPBH-UHFFFAOYSA-N C=1C(N=NC=2C=CC(=CC=2)S(O)(=O)=O)=C(O)C(N=NC=2C=CC(=CC=2)S(O)(=O)=O)=C(O)C=1C(O)C1=CC=CC=C1 Chemical compound C=1C(N=NC=2C=CC(=CC=2)S(O)(=O)=O)=C(O)C(N=NC=2C=CC(=CC=2)S(O)(=O)=O)=C(O)C=1C(O)C1=CC=CC=C1 FWBBZLMJJAUPBH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101001072067 Homo sapiens Proprotein convertase subtilisin/kexin type 4 Proteins 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 108010022052 Proprotein Convertase 5 Proteins 0.000 description 1
- 102100036371 Proprotein convertase subtilisin/kexin type 4 Human genes 0.000 description 1
- 102100036365 Proprotein convertase subtilisin/kexin type 5 Human genes 0.000 description 1
- 102100038946 Proprotein convertase subtilisin/kexin type 6 Human genes 0.000 description 1
- 101710180552 Proprotein convertase subtilisin/kexin type 6 Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LDESLTJTFMRNCR-UHFFFAOYSA-H chromium(3+) trisulfate octahydrate Chemical compound O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cr+3].S(=O)(=O)([O-])[O-].S(=O)(=O)([O-])[O-].[Cr+3] LDESLTJTFMRNCR-UHFFFAOYSA-H 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/04—Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/22—Trisazo dyes of the type A->B->K<-C
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
Definitions
- the present invention relates to new azo dyestuffs which are particularly interesting for the dyeing or finishing of leathers.
- R represents a hydrogen atom or an alkyl or aryl group
- a 1 , A 2 and A 3 each represent the residue of a diazotisable aromatic primary amine, which may be the same or different, with at least one of the residues containing at least one sulphonic or carboxylic acid group
- n is zero or 1 and the nucleus B is unsubstituted or substituted by one or two nitro, hydroxy or water-solubilising groups.
- Suitable water-solubilising groups are the sulpho and carboxy groups.
- the invention includes dyestuffs of formula (I) and their metalliferous complexes in the form of their salts with amines or ammonium compounds.
- the dyestuffs of formula (I), in which n is zero, can be prepared for example by coupling the diazo derivative of an aromatic primary amine or the diazo derivative of two amines of this type with a coupling compound of the formula: ##SPC5##
- the dyestuffs of formula (I), in which n is zero and A 1 and A 2 are different, may for example be advantageously prepared by successively coupling the diazo derivatives of amines A 1 --NH 2 and A 2 --NH 2 . The couplings take place in the ortho position to the hydroxy groups.
- the dyestuffs of formula (I), in which n equals 1, can be prepared for example by coupling a coupling compound of formula (II) with the diazo derivative of an aromatic primary amine A 1 --NH 2 , having a coupling position at the rate of one molecule of amine to each molecule of coupling compound, and then by coupling the monoazo dye thus obtained with the diazo derivative of a diazotisable aromatic primary amine or the diazo derivatives of two amines of this type.
- the dyestuffs of formula (I), in which n equals 1 and A 2 and A 3 represent different residues, may for example be advantageously prepared by successively coupling the diazo derivatives of the amines A 2 --NH 2 and A 3 --NH 2 .
- the amines A 1 --NH 2 , A 2 --NH 2 and A 3 --NH 2 may belong to the most diverse series, such as for example the benzene, naphthalene, and heterocyclic or azo series, and have up to three substituents. At least one of these amines must have at least one carboxylic or sulphonic acid group. Other substituents are, for example, halogen atoms, methyl, ethyl, hydroxy, methoxy, ethoxy, carboxy-methoxy, amino, acetylamino, oxalylamino or nitro groups.
- the coupling compounds of formula (II) can be prepared, for example, by condensing resorcinol in an alkaline medium with a compound of the formula: ##SPC6##
- the dyestuffs of formula (I) are water-soluble. They dye leathers from different tanning processes in shades of brown, which are bright and very fast, particularly to light, wet tests, solvents and to mechanical actions.
- the dyestuffs of formula (I), in which one of the residues A 1 or A 2 has a group in the ortho position to the azo linkage capable of taking part in the formation of a complex, for example a hydroxy, amino, alkoxy, carboxy or OCH 2 --COOH group can be converted into metalliferous complexes containing one or less than one atom of metal to each molecule of dyestuff.
- the metal can be, for example, iron, copper, chromium, cobalt or nickel.
- the conversion into a metalliferous complex can be effected for example by any process of metallization in an aqueous medium or in a mixture of water and organic solvent such as alcohol, polyol, formamide or dimethylformamide, at a temperature between 10° and 150°C. and at a pH of between 1 and 11, preferably between 5 and 8.
- metallizing agents are metal chlorides, fluorides, acetates, sulphates, oxides and hydroxides, as well as alkali metal chromates and dichromates.
- the dyestuffs of formula (I) and their metalliferous complexes can be converted into salts by means of an amine or a quaternary ammonium salt.
- suitable amines are arylguanidines, cyclohexylamine or dicyclohexylamine.
- the salts obtained are insoluble in water, but are soluble in organic solvents, in particular in alcohols and diols.
- suitable ammonium salts are dimethyl benzyl alkyl ammonium chlorides, acetates or sulphates and 2'-hydroxy-ethyl trimethylammonium chloride.
- the salified derivatives can be used for the colour finishing of leather, for example for the aniline finishing of skins either previously dyed or undyed, and the finishing of leathers with a buffed or artificial hair side and the spray-gun dyeing of full grain leathers, on which they give transparent shades, which are very bright and very fast, particularly to light and wet rubbing.
- the same dye is obtained if, in 30 minutes, the diazo derivative of 34.6 parts of p-sulphanilic acid is added to a solution at pH 11 and at 5°C., of 21.6 parts of 2,4-dihydroxy-benzhydrol in 400 parts of water, to which 45 parts of sodium carbonate has been added.
- the disazo dyestuffs are obtained by coupling the 2,4-dihydroxy-benzhydrol firstly with the diazo derivatives of the amino A 1 --NH 2 then by coupling the dyestuff thus obtained with the diazo derivative of the amine A 2 --NH 2 .
- Example 10 If, in Example 10, the 4,6-dinitro-2-amino-phenol is replaced by 12.3 parts of 2-methoxy aniline and the 4-nitro aniline by 30.9 parts of 4-amino-4'-nitro-diphenylamine-2'-sulphonic acid, one obtains a dyestuff which dyes leathers from different tanning processes in shades which are much more yellow.
- Example 14 69.3 parts of the copper complex described in Example 14 (monosodium salt) are dissolved in 2000 parts of water at 60°C. Then, 23.9 parts of di-ortho-tolylguanidine in solution in 250 parts of water and 11 parts of 10N hydrochloric acid are added in an hour. The dyestuff in the form of an amine salt is filtered, washed in water and dried. It is totally insoluble in water but easily soluble in alcohols such as ethanol and in the monomethyl ether of ethylene glycol. The alcoholic solutions, when diluted, are violet-brown.
- a sample of 100 parts of shaved clear chorme box calf is rinsed, neutralised and then rinsed again.
- This leather is placed in a fulling machine containing a solution of 1 part of the dyestuff of Example 10 in 500 parts of water at 60°C. It is fulled for 45 minutes at 60°C. then a tawing paste suspended in 50 parts of water is added by means of a dispersing agent and the leather is fulled for another 30 minutes.
- the box calf is dyed a deep red brown shade, which is fast to light, washing and solvents.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR71.01106 | 1971-01-14 | ||
| FR7101106A FR2121446B1 (enrdf_load_stackoverflow) | 1971-01-14 | 1971-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3943122A true US3943122A (en) | 1976-03-09 |
Family
ID=9070263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/217,950 Expired - Lifetime US3943122A (en) | 1971-01-14 | 1972-01-14 | Polyazo compounds containing benzhydrol as a component |
Country Status (11)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4508926A (en) * | 1982-12-28 | 1985-04-02 | Richter Gedeon Vegyeszeti Gyar Rt. | 4-Hydroxy-benzhydrols, process for their preparation and pharmaceutical compositions containing them |
| US4510338A (en) * | 1982-12-28 | 1985-04-09 | Richter Gedeon Vegyeszeti Gyar Rt. | Resorcin derivatives, process for their preparation and pharmaceutical compositions containing them |
| WO2006064852A1 (ja) * | 2004-12-16 | 2006-06-22 | Mitsubishi Chemical Corporation | アゾ色素、これを用いた異方性色素膜用組成物、異方性色素膜および偏光素子 |
| WO2006069929A2 (en) | 2004-12-29 | 2006-07-06 | Ciba Specialty Chemicals Holding Inc. | Dyes that are soluble in organic solvents |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2018234A (en) * | 1932-07-26 | 1935-10-22 | Du Pont | Azo dye and method for its preparation |
| US2061545A (en) * | 1933-09-15 | 1936-11-24 | Firm Of J R Geigy A G | Conversion products of azo dyestuffs and their production |
| US2259735A (en) * | 1939-10-31 | 1941-10-21 | American Cyanamid Co | Metallized acid polyazo dyes |
| US2394114A (en) * | 1940-05-15 | 1946-02-05 | Gen Aniline & Film Corp | Trisazo diphenyl dyestuffs |
| US2750375A (en) * | 1951-12-24 | 1956-06-12 | Hoechst Ag | Polyazo-dyestuffs |
| FR1503833A (fr) * | 1965-10-15 | 1967-12-01 | Sandoz Sa | Colorants polyazoïques, leur procédé de fabrication et leurs applications |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1165637A (fr) * | 1955-12-17 | 1958-10-28 | Hoechst Ag | Colorants azoïques et procédé pour leur préparation |
-
1971
- 1971-01-14 FR FR7101106A patent/FR2121446B1/fr not_active Expired
- 1971-12-16 BE BE776830A patent/BE776830A/xx unknown
- 1971-12-17 NL NL7117330A patent/NL7117330A/xx unknown
-
1972
- 1972-01-12 CH CH39672A patent/CH539107A/fr not_active IP Right Cessation
- 1972-01-13 ES ES398858A patent/ES398858A1/es not_active Expired
- 1972-01-13 DE DE19722201512 patent/DE2201512A1/de active Pending
- 1972-01-13 GB GB161372A patent/GB1379971A/en not_active Expired
- 1972-01-14 US US05/217,950 patent/US3943122A/en not_active Expired - Lifetime
- 1972-01-14 AR AR240082A patent/AR192338A1/es active
- 1972-01-14 BR BR217/72A patent/BR7200217D0/pt unknown
- 1972-01-14 IT IT67109/72A patent/IT958678B/it active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2018234A (en) * | 1932-07-26 | 1935-10-22 | Du Pont | Azo dye and method for its preparation |
| US2061545A (en) * | 1933-09-15 | 1936-11-24 | Firm Of J R Geigy A G | Conversion products of azo dyestuffs and their production |
| US2259735A (en) * | 1939-10-31 | 1941-10-21 | American Cyanamid Co | Metallized acid polyazo dyes |
| US2394114A (en) * | 1940-05-15 | 1946-02-05 | Gen Aniline & Film Corp | Trisazo diphenyl dyestuffs |
| US2750375A (en) * | 1951-12-24 | 1956-06-12 | Hoechst Ag | Polyazo-dyestuffs |
| FR1503833A (fr) * | 1965-10-15 | 1967-12-01 | Sandoz Sa | Colorants polyazoïques, leur procédé de fabrication et leurs applications |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4508926A (en) * | 1982-12-28 | 1985-04-02 | Richter Gedeon Vegyeszeti Gyar Rt. | 4-Hydroxy-benzhydrols, process for their preparation and pharmaceutical compositions containing them |
| US4510338A (en) * | 1982-12-28 | 1985-04-09 | Richter Gedeon Vegyeszeti Gyar Rt. | Resorcin derivatives, process for their preparation and pharmaceutical compositions containing them |
| WO2006064852A1 (ja) * | 2004-12-16 | 2006-06-22 | Mitsubishi Chemical Corporation | アゾ色素、これを用いた異方性色素膜用組成物、異方性色素膜および偏光素子 |
| US20090267031A1 (en) * | 2004-12-16 | 2009-10-29 | Mitsubishi Chemical Corporation | Azo dye, composition containing the same for anisotropic dye film, anisotropic dye film, and polarizing element |
| US7960521B2 (en) | 2004-12-16 | 2011-06-14 | Mitsubishi Chemical Corporation | Azo dyes, compositions for anisotropic dye films using them, anisotropic dye films and polarizing elements |
| WO2006069929A2 (en) | 2004-12-29 | 2006-07-06 | Ciba Specialty Chemicals Holding Inc. | Dyes that are soluble in organic solvents |
| WO2006069929A3 (en) * | 2004-12-29 | 2006-11-23 | Ciba Sc Holding Ag | Dyes that are soluble in organic solvents |
| US20080184497A1 (en) * | 2004-12-29 | 2008-08-07 | Thomas Ruch | Dyes That are Soluble in Organic Solvents |
| US7517369B2 (en) | 2004-12-29 | 2009-04-14 | Ciba Specialty Chemicals Corporation | Dyes that are soluble in organic solvents |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2121446A1 (enrdf_load_stackoverflow) | 1972-08-25 |
| DE2201512A1 (de) | 1972-07-27 |
| BE776830A (fr) | 1972-06-16 |
| ES398858A1 (es) | 1975-06-16 |
| BR7200217D0 (pt) | 1973-06-12 |
| NL7117330A (enrdf_load_stackoverflow) | 1972-07-18 |
| FR2121446B1 (enrdf_load_stackoverflow) | 1974-03-22 |
| GB1379971A (en) | 1975-01-08 |
| CH539107A (fr) | 1973-07-15 |
| IT958678B (it) | 1973-10-30 |
| AR192338A1 (es) | 1973-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: PRODUITS CHIMIQUES UGINE KUKLMANN TOUR MANHATTAN L Free format text: CHANGE OF NAME;ASSIGNOR:CHARLES DAVENPORT;REEL/FRAME:004245/0711 Effective date: 19831116 |
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| AS | Assignment |
Owner name: PRODUITS CHIMIQUES UGINE KUHLMANN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:PECHINERY UGINE KUHLMANN;REEL/FRAME:004319/0683 Effective date: 19840820 Owner name: PECHINEY UGINE KUHLMANN Free format text: MERGER;ASSIGNOR:UGINE KUHLMANN;REEL/FRAME:004319/0671 Effective date: 19840820 |